The Journal of organic chemistry

Mechanistic studies on the cis to trans epimerization of trisubstituted 1, 2, 3, 4-tetrahydro-β-carbolines

ML Van Linn, JM Cook

Index: Van Linn, Michael L.; Cook, James M. Journal of Organic Chemistry, 2010 , vol. 75, # 11 p. 3587 - 3599

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Citation Number: 21

Abstract

It is well-known that N b-benzyltryptophan alkyl esters undergo the Pictet− Spengler reaction with aldehydes to furnish both cis-and trans-1, 2, 3, 4-tetrahydro-β-carbolines, with the trans isomer predominating. Epimerization at C-1 took place under acidic conditions to produce, exclusively, the thermodynamically more stable trans diastereomer via internal asymmetric induction. Recent kinetic experiments provided insight into the cis to trans epimerization ...